


Baltimore Prison Blues

by maydaysmusings



Series: Another Time, Another Place (But Always With You) [1]
Category: House M.D.
Genre: 50's!Au, Crossdressing, Crossdressing!Kink, M/M, Porn, Porn With Plot, Smut, cell!sex, crossdressing!wilson, easter egg for my girlfriend, i didn't put it in the psych fandom bc the characters are barely there, non-injured!house, panty!kink, prison!au, wilson in panties
Language: English
Status: Completed
Published: 2019-06-11
Updated: 2019-06-11
Packaged: 2020-04-24 05:26:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,592
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19166704
Author URL: https://archiveofourown.org/users/maydaysmusings/pseuds/maydaysmusings
Summary: When Greg winds up in jail, due to a bar brawl, James comes three times. Once for comfort, once to rescue and once just for fun.





	Baltimore Prison Blues

**_Baltimore County Jail_ **

**_Baltimore, Maryland_ **

**_June 8th, 1956_ **

Greg sighs and thumps his head back against the cinder blocks of his cell wall. All of this because of a little bar brawl? Surely, it has to be overkill. He looks out of the bars at the cinderblocks of the hallway. Couldn’t even get a nicer paint job? He picks at his blue uniform, before his ears perk at the sounds of an argument near the front desk, just around the corner from the hallway.

“Please, I have to see him. The fight was all my fault, Sir! I swear it!” The voice pleads, slightly feminine, but with a manly texture. Greg’s brow furrows as he listens more. There was no lady there to start the fight he was in.

“Ma’am, I cannot permit you to go back there until he is processed. Then, we will contact his next of kin and if you are permitted, you can come see him.”

“He shouldn’t be in there! He didn’t do anything!”

“He could’ve killed someone. The men are pressing charges.”

“Please, just let me talk to him. I’ll leave after and never come back.”

“…You got half an hour, sweetie,” the man gruffs and then there’s footsteps coming down the hall. The man, Sheriff Henry Spencer, opens the cell and lets the woman in, “No funny stuff,” then leaves, locking it behind him.

Greg looks up at the woman, except, it’s no woman at all. “Jimmy?” He breathes, eyes looking him over, the black pumps, long, smooth legs, leading up to the matching, black with blue polka-dots halter dress, which belonged to his little sister, Lulu. But, this was not his sister. The toner arms, broader shoulders, the telling curve of the lips he’d kissed so many times before, but never in that shade of pink, the too big sunglasses and cheap brown wig, the framed the slightly rounded face of Greg’s lover, James Wilson.

“Hi, Greggy,” he purrs, pulling off the glasses, his brown eyes twinkling, covered in thick liner and mascara. “You look even better than I imagined.” He hums, straddling him.

“What are you doing here? Dressed like that?” He whispers, touching James’ cheek.

“Couldn’t let my baby be all alone in his cell, now could I?" He pouts. "Your sister helped me get ready. Knew I had to see you,” he leans in for a kiss, that’s reciprocated immediately and desperately.

“You’re so pretty, Jimmy,” he groans softly and runs his hands up his thighs, gasping as he feels the silk and lace underneath the dress. “Are you…”

“You always said you wanted to see me in some. I stole some the other night.” He gasps as he feels the rough fingers tug at them, groping him through them. “I just didn’t think the opportunity to wear them would come so soon.”

He leans in to kiss at James’ neck, sucking softly as he palms his cock through the panties, his own straining against the tight pants they gave him. “I can’t wait to see you riding me in them,” he whispers, running his hands up his sides, now.

“I even prepped before I came,” he smirks. “So you can just slide right in.” He gasps as Greg reaches and unties the halter, letting it and two pieces of padding, standing in for boobs, fall. “Like what you see?”

“Always,” he growls and leans in, sucking at his nipple harshly, flicking his tongue.

James moans and tugs his hair, panting softly, “Knew you would,” he smirks proudly and rocks his hips a little, groaning as he feels how hard Greg is. “We should take care of your little problem, huh?”

“We will,” he rasps, switching to suck on the other nub, hands slipping back down to grip James’ ass. He flicks his tongue and tugs gently before pulling off, “Stand up.”

James stands, biting his lip, then gasping loudly as Greg rips the dress down, thankfully not ruining it, pooling it at James’ feet, leaving him exposed in just his wig, make-up, panties and pumps.

“God, look at you. All dressed for me and my cock.” He palms himself, “Turn around for me.” He groans as James does, “Now, bend over.” He unzips and gropes himself, watching James’ ass stretch the smooth silk, lace clutching his thighs tightly. “You look so pretty like this, baby.” He reaches out, snapping the waistband of the panties, causing Wilson to jump with a whimper. “Kneel in front of me.”

Happy to oblige, Wilson steps out of the dress on the floor and walks over, carefully kneeling for him, “Yes, Sir?” He looks up with wide, innocent eyes, licking his lips.

“Open that pretty little mouth.” He hums and smirks, pulling himself out and slotting himself between the ever obedient lips of his Jimmy, letting him suckle on the head, “That’s it. That’s a good boy.” He cradles the back of his head before groaning as James takes over, sucking him down halfway, “Shit, Jimmy,” he whines.

James smirks around him, bobbing his head slowly, sucking hard with hollowed cheeks, eyes flickering up to look at Greg through his lashes. He moans around him, knowing the vibrations always do something wicked to Greg. He continues bobbing and sucking for a few minutes, loving the choked off moans and whimpers coming from above him, before finally deep throating him. He forces his gag reflex to not go off and holds him down his throat, Greg’s cock twitching in it before he has to pull off for air, jerking him instead.

Greg growls and jerks his chin up, locking eyes with him, “Mmm, look at this. Lipstick smeared on my cock, your lips all swollen…so fuckable,” he grunts. “Let’s get to that, shall we?” He lets go off his chin to pull him up from the floor, “Want you to ride me.”

“Mmm, don’t I always?” He smirks and slips the panties to the side and straddles him, positioning Greg’s cock at his entrance and sliding down slowly. He whimpers as he gets fully seated and kisses Greg hard, tangling a hand in his hair.

Sliding his hands to his ass, Greg sucks on his bottom lip, tugging at it, kneading his cheeks before a small thrust. He pulls back from the kiss and attaches his mouth to his neck, sucking on it as James starts to lift his hips, then let them drop, riding him slowly. “You know I don’t mind going slow, but you don’t have much longer in here, sweetheart.” He nips his earlobe and tugs it.

James whines softly and starts to bounce, arching into him slightly, “I know. You owe me a nice, slow fuck when you get out of here.” He drags his nails down the back of his neck lightly, smirking to himself, before starting to ride him fast, clenching tight around him, just how Greg liked it.

“Always so perky for me,” Greg ducks his head to suck at his nipples, first one, toying with it to draw the squeaky moans out of his lover, then the other to intensify them. He kisses back up, sucking at his neck again, making little dark marks that the halter had no way of hiding, and he knew it.

“Greg, that’s gonna get me in trouble,” he grips his hair, but instead of pulling him off, he holds him there, whining softly. He starts to bounce faster, panting and squeaking out moans, “Feels so good.”

“You always feel good, especially your hole, around my cock,” he growls against his neck and licks a long stripe up it, bucking his hips with a slight angle, smirking at the choked off gasp coming from above him, the nails digging into his skin as the cock twitch against his stomach. “There it is,” he grips James’ hips, plants his feet and starts fucking up into him roughly, chuckling as James ducks his head down and bites his neck hard to muffle his cries. “Yeah, that’s it,” he grunts, pounding into James.

“Greggy,” he whines in his ear, high and desperate, “Gotta cum!” He mewls and sucks on Greg’s earlobe, thighs shaking a bit.

“Do it. Mess up those pretty little panties,” He gives his ass a firm smack and Wilson gasps a cry as he cums hard a few seconds later, into the silk confines of his underwear. “Good boy,” he grunts and pounds up, nails digging into his hips before he’s emptying his load into James’ hole, groaning his name. He pants and slows his thrusts, kissing him softly, mumbling against his lips, “Thank you, Jimmy.”

James grins and kisses him again, pressing their foreheads together, “Of course, Greggy,” he gives one last squeeze of cock, before he slides off him and situates the panties back in place. “Should get going.” He zips up Greg’s pants for him and kisses him before he redresses, making sure everything’s in place and calling for the sheriff. “Carlton will be back in town tomorrow. He said he’d come get you out,” he hums and winks as he’s escorted out of the cell, tossing a harmonica through the bars from his purse.

Greg smirks and catches it, “Always coming to my rescue, Jimmy.” He chuckles and puts it to his lips, starting to play a bluesy tune, singing low and raspy as he pauses, “I hear the train a comin,…it’s rolllin’ ‘round the bend and I ain’t seen the sunshine since, I don’t know when…I’m stuck in Baltimore Prison and time keeps draggin’ on…”


End file.
